4-Methylmorpholine → HCID 66843074, Verbindung

HRID 254046

Reaktionsgleichung

Reaktionsgleichung von HRID 254046
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][C:37]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[O:38])[C@H:31]2[C:46]2[CH:60]=[CH:59][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56](O)=[O:57])=[O:53])=[CH:48][CH:47]=2)=[CH:26][CH:25]=1.CN1CCOCC1.[NH2:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71]>C(Cl)Cl>[F:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][CH:37]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[OH:38])[C@H:31]2[C:46]2[CH:47]=[CH:48][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56]([NH:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71])=[O:57])=[O:53])=[CH:59][CH:60]=2)=[CH:28][CH:29]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6950340D-tert-leucineHCID 66842760N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio)-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine

Produkt 1

HCID 66843074HCID 66843074, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TBTU (0.021 g, 0.067 mmol) was added to a solution of N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (0.030 g, 0.056 mmol) and N-methyl morpholine (0.017 g, 0.166 mmol) in CH2Cl2 (5 ml) at 30° C. After 1.5 h, D-tert-leucine (0.011 g, 0.083 mmol) was added. Full conversion to the corresponding amide was obtained after 30 minutes. The reaction was quenched by the addition of water (1 ml). After 10 minutes, MeOH (3 ml) and NaBH (0.042 g, 1.11 mmol) were added. After 5 minutes, the reaction was quenched by the addition of 0.1M NH4OAc buffer (1 ml). The reaction mixture was concentrated and purified by preparative HPLC using an eluent of 0-50% CH3CN in 0.1M N4OAc buffer. The title compound (0.025 g, 69%) was obtained as a colourless solid. M/z: 654.0 (M−1). 1H NMR [(CD3)2SO), 400 MHz] δ 0.86 (s, 9H), 2.82-2.98 (m, 2H), 3.76-3.81 (m, 2H), 3.92-3.96 (m, 1H), 4.26-4.33 (m, 1H), 4.52 (s, 2H), 4.68-4.76 (m, 1H), 5.02-5.07 (m, 1H), 6.97-7.37 (m, 12H), 7.58-7.63 (m, 1H), 8.29-8.34 (m, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-e4483cf9cb864021a1d764efc7cf135a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07871998B2

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